Question
Fri February 01, 2013 By:

acidic nature of carboxylic acid

Expert Reply
Fri February 01, 2013

In carboxylic acids, the same bond gets broken - the bond between the hydrogen and oxygen in an -OH group. Writing the rest of the molecule as "X":

Ethanoic acid has the structure:

The acidic hydrogen is the one attached to the oxygen. When ethanoic acid ionises it forms the ethanoate ion, CH3COO-.

You might reasonably suppose that the structure of the ethanoate ion was as below, but measurements of bond lengths show that the two carbon-oxygen bonds are identical and somewhere in length between a single and a double bond.

The more you can spread charge around, the more stable an ion becomes. In this case, if you delocalise the negative charge over several atoms, it is going to be much less attractive to hydrogen ions - and so you are less likely to re-form the ethanoic acid.
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